6-乙炔基薁 | 319431-53-3

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 中文名称: 6-乙炔基薁
• 英文名称: 6-ethynylazulene
• CAS: 319431-53-3
• 化学式: C₁₂H₈
• 分子量: 152.196
• InChiKey: NEPBPTLWUWIANH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  6-乙炔基薁 在 氧气 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以86%的产率得到di(6-azulenyl)diacetylene
  参考文献：
  名称：

  Synthesis and Redox Behavior of Azulene-Substituted Benzene Derivatives and (η⁵-Cyclopentadienyl)[tetra- and di(6-azulenyl)cyclobutadiene]cobalt Complexes

  摘要：

  1,2-Di(6-azulenyl)tetraphenylbenzenes and (6-azulenyl)pentaphenylbenzenes were synthesized by Diels-Alder reactions of di(6-azulenyl)acetylenes and 6-(phenylethynyl)azulenes with tetraphenylcyclopentadienone. Cobalt-mediated cyclooligomerization of mono- and di(6-azulenyl)acetylenes afforded 1,3,5- and 1,2,4-tri(6-azulenyl)benzene derivatives together with (eta (5)-cyclopentadienyl)[tetra- and di(6-azulenyl)cyclobutadiene] cobalt complexes. The redox behavior of these novel (6-azulenyl)benzene derivatives and [tetra- and di(6-azulenyl)cyclobutadiene] cobalt complexes was examined by cyclic voltammetry (CV). Mono(6-azulenyl)benzenes exhibited a reduction wave upon CV. In contrast, 1,2-di(6-azulenyl)benzenes showed a two-step reduction wave at the similar potential region upon CV, which revealed the formation of a dianion stabilized by 6-azulenyl substituents under electrochemical reduction conditions. Three 6-azulenyl substituents on benzene in a 1,2,4 relationship also increased electron-accepting properties because of the formation of a closed-shell dianionic structure, whereas 1,3,5-tri(6-azulenyl)benzenes were reduced stepwise.

  DOI：

  10.1021/jo010540u
• 作为产物：
  描述：

  6-溴薁 在 bis-triphenylphosphine-palladium(II) chloride potassium fluoride 、 copper(l) iodide 、 水 、 三乙胺 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 5.5h， 生成 6-乙炔基薁
  参考文献：
  名称：

  Diels–Alder approach to the synthesis of azulene-substituted benzene derivatives. Synthesis and redox behavior of 1,2-di(6-azulenyl)tetraphenylbenzenes

  摘要：

  1,2-Di(6-azulenyl)tetraphenylbenzenes and (6-azulenyl)pentaphenylbenzenes were synthesized by Diels-Alder reaction of di(6-azulenyl)acetylenes and 6-(phenylethynyl)azulenes with tetraphenylcyclopentadienone. Mono(6-azulenyl)benzenes exhibited a reduction wave upon cyclic voltammetry (CV). In contrast to the benzene derivatives, di(6-azulenyl)benzenes showed a two-step reduction wave at similar potential region upon CV, which revealed the formation of dianions stabilized by 6-azulenyl substituents under electrochemical reduction conditions. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01445-3

文献信息

• Diels–Alder approach to the synthesis of azulene-substituted benzene derivatives. Synthesis and redox behavior of 1,2-di(6-azulenyl)tetraphenylbenzenes
  作者：Shunji Ito、Haruki Inabe、Testuo Okujima、Noboru Morita、Masataka Watanabe、Kimiaki Imafuku

  DOI：10.1016/s0040-4039(00)01445-3

  日期：2000.10

  1,2-Di(6-azulenyl)tetraphenylbenzenes and (6-azulenyl)pentaphenylbenzenes were synthesized by Diels-Alder reaction of di(6-azulenyl)acetylenes and 6-(phenylethynyl)azulenes with tetraphenylcyclopentadienone. Mono(6-azulenyl)benzenes exhibited a reduction wave upon cyclic voltammetry (CV). In contrast to the benzene derivatives, di(6-azulenyl)benzenes showed a two-step reduction wave at similar potential region upon CV, which revealed the formation of dianions stabilized by 6-azulenyl substituents under electrochemical reduction conditions. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Synthesis and Redox Behavior of Azulene-Substituted Benzene Derivatives and (η⁵-Cyclopentadienyl)[tetra- and di(6-azulenyl)cyclobutadiene]cobalt Complexes
  作者：Shunji Ito、Haruki Inabe、Tetsuo Okujima、Noboru Morita、Masataka Watanabe、Nobuyuki Harada、Kimiaki Imafuku

  DOI：10.1021/jo010540u

  日期：2001.10.1

  1,2-Di(6-azulenyl)tetraphenylbenzenes and (6-azulenyl)pentaphenylbenzenes were synthesized by Diels-Alder reactions of di(6-azulenyl)acetylenes and 6-(phenylethynyl)azulenes with tetraphenylcyclopentadienone. Cobalt-mediated cyclooligomerization of mono- and di(6-azulenyl)acetylenes afforded 1,3,5- and 1,2,4-tri(6-azulenyl)benzene derivatives together with (eta (5)-cyclopentadienyl)[tetra- and di(6-azulenyl)cyclobutadiene] cobalt complexes. The redox behavior of these novel (6-azulenyl)benzene derivatives and [tetra- and di(6-azulenyl)cyclobutadiene] cobalt complexes was examined by cyclic voltammetry (CV). Mono(6-azulenyl)benzenes exhibited a reduction wave upon CV. In contrast, 1,2-di(6-azulenyl)benzenes showed a two-step reduction wave at the similar potential region upon CV, which revealed the formation of a dianion stabilized by 6-azulenyl substituents under electrochemical reduction conditions. Three 6-azulenyl substituents on benzene in a 1,2,4 relationship also increased electron-accepting properties because of the formation of a closed-shell dianionic structure, whereas 1,3,5-tri(6-azulenyl)benzenes were reduced stepwise.